$113+ Cheap flights from Chicago (CHI) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jan 15 — Jan 221
1 adult, Economy
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Cheapest flights from Chicago to JamaicaExplore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.
This American Airlines deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/184:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/13![American Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:30 amORD - MBJ
1 stop7h 43mDelta
Thu 12/1812:35 pmMBJ - ORD
1 stop7h 08mDelta
Deal found 12/13![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:00 amMDW - MBJ
1 stop6h 04mDelta
Thu 12/1812:35 pmMBJ - MDW
1 stop12h 12mDelta
Deal found 12/13![Delta logo]()
$391
This Frontier deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amORD - MBJ
1 stop7h 24mFrontier
Tue 12/303:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 12/16![Frontier logo]()
$392
This Delta deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:45 amORD - MBJ
1 stop6h 28mDelta
Tue 12/238:00 amMBJ - ORD
2 stops13h 36mDelta
Deal found 12/14![Delta logo]()
$396
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - MBJ
1 stop25h 59mFrontier
Wed 12/243:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/14![Frontier logo]()
$410
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mFrontier
Wed 12/2410:24 amMBJ - MDW
1 stop12h 48mFrontier
Deal found 12/14![Frontier logo]()
$410
This Frontier deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amORD - MBJ
1 stop7h 24mFrontier
Wed 12/313:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/16![Frontier logo]()
$413
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:55 pmORD - MBJ
1 stop14h 10mDelta
Wed 12/2412:30 pmMBJ - ORD
1 stop8h 08mDelta
Deal found 12/15![Delta logo]()
$421
This Priceline deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amORD - MBJ
1 stop7h 24mFrontier
Mon 12/2910:14 amMBJ - ORD
1 stop13h 10mFrontier
Deal found 12/16![Frontier logo]()
$433
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:15 amORD - MBJ
1 stop29h 40mFrontier
Mon 12/2910:14 amMBJ - ORD
1 stop13h 10mFrontier
Deal found 12/14![Frontier logo]()
$435
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - MBJ
1 stop26h 45mFrontier
Tue 12/233:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/14![Frontier logo]()
$445
Find flight deals from Chicago to Jamaica
Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated December 16, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $337 (Expedia) |
One-way from | $113 (Super.com) |
Popular in | March |
Cheapest in | January |
Average price | $617 |
Good round-trip deal | $459 or less |
Good one-way deal | $215 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 16, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.
Fly from
Chicago
Fly to
Jamaica
Route
Depart
Return
Price
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Thu 1/29
8:43 pm-12:12 pm
1 stop14h 29m
Kingston Norman Manley
Mon 2/2
1:17 pm-11:47 pm
1 stop11h 30m
$337
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Mon 2/2
5:15 am-12:12 pm
1 stop5h 57m
Kingston Norman Manley
Thu 2/5
1:17 pm-11:46 pm
1 stop11h 29m
$337
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Sun 2/1
4:38 pm-12:12 pm
2 stops18h 34m
Kingston Norman Manley
Mon 2/9
1:17 pm-11:46 pm
1 stop11h 29m
$386
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 1/18
6:45 am-3:20 pm
1 stop7h 35m
Montego Bay Sangster Intl
Wed 1/21
4:45 pm-10:22 pm
1 stop6h 37m
$391
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 2/17
6:00 am-3:19 pm
1 stop8h 19m
Montego Bay Sangster Intl
Tue 2/24
4:44 pm-10:44 pm
1 stop7h 00m
$391
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 3/15
5:38 pm-10:10 am
1 stop16h 32m
Montego Bay Sangster Intl
Thu 3/19
4:55 pm-9:55 am
1 stop17h 00m
$391
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 1/28
6:00 am-3:20 pm
1 stop8h 20m
Montego Bay Sangster Intl
Wed 2/4
4:45 pm-10:22 pm
1 stop6h 37m
$391
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 3/16
7:56 pm-10:10 am
1 stop14h 14m
Montego Bay Sangster Intl
Thu 3/19
2:25 pm-9:25 am
1 stop19h 00m
$391
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 1/20
7:30 pm-12:32 pm
1 stop16h 02m
Montego Bay Sangster Intl
Fri 1/30
12:38 pm-6:49 pm
1 stop7h 11m
$391
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 1/18
5:30 am-12:54 pm
1 stop6h 24m
Montego Bay Sangster Intl
Wed 1/28
12:38 pm-11:56 pm
1 stop12h 18m
$391
Showing 1-10 of 49 results
Best time to book a flight from Chicago to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Jamaica
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $193). Flying from Chicago to Jamaica in March is currently the most expensive (average of $408). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to JM?
Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.
A simple way to save on the total cost of your ticket is to fly from Chicago to Jamaica in the afternoon. If you’re flexible enough to do this you can expect to save up to 65% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Chicago to Jamaica?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated December 16, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Jamaica
Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 16, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$415 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$186 | Average$706 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$341 | Average$662 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$356 | Average$601 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$433 | Average$671 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$549 | Average$724 | FlexibilityNo cancel fee | On-time63% |